Aniline → 1-amino-N-(5-((3-(2-cyanopropan-2-yl)phenyl)carbamoyl)-2-methylphenyl)isoquinoline-5-carboxamide

HRID 1051256Notes

Reaction equation

HRID 1051256 reaction equation
C([NH:5][C:6]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]([NH:18][C:19]3[CH:24]=[C:23]([C:25](=[O:37])[NH:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29](C(F)(F)F)[CH:28]=4)[CH:22]=[CH:21][C:20]=3[CH3:38])=[O:17])[C:10]=2[CH:9]=[CH:8][N:7]=1)(C)(C)C.NC1C=[C:42]([C:46](C)([CH3:49])[C:47]#[N:48])C=CC=1.NC1C=CC=CC=1>>[NH2:5][C:6]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]([NH:18][C:19]3[CH:24]=[C:23]([C:25](=[O:37])[NH:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:46]([C:47]#[N:48])([CH3:49])[CH3:42])[CH:28]=4)[CH:22]=[CH:21][C:20]=3[CH3:38])=[O:17])[C:10]=2[CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 3

HCID 6115AnilineHCID 569657872-(3-Aminophenyl)-2-methylpropanenitrileHCID 1180907961-(t-butylamino)-N-(2-methyl-5-((3-(trifluoromethyl)phenyl)carbamoyl)phenyl)isoquinoline-5-carboxamide

Product 1

HCID 1180907931-amino-N-(5-((3-(2-cyanopropan-2-yl)phenyl)carbamoyl)-2-methylphenyl)isoquinoline-5-carboxamideYield 20%

Procedure

The procedures of Steps (1), (2) and (3) of Example 2 and Step (4) of Example 1 were repeated step by step, except for using 2-(3-aminophenyl)-2-methylpropanenitrile obtained in Step (2) above instead of aniline in Step (1) of Example 2 to obtain the title compound (14 mg, 20%).

Sources & evidence

ORD record
ord-6cf413f69d9a4cf19db7df06d9f01f02
Source dataset
uspto-grants-2016_07
Patent number
US09388165B2

Reaction notes

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